Vacation rentals in Middletown

Western Mine Retreat near wine country

This private vacation retreat is located just 20 minutes from Calistoga in Middletown, CA. Decorated in a rustic mining-theme after the historic area, this large living space is enhanced by a 60'x15' covered deck with relaxing views of the woods and a pond just down the hill. Amenities include high speed WiFi, a large smart television, and game tables. Nearby attractions include wine tasting, hot springs resorts, quaint downtown Middletown, and the Twin Pines Casino (just down the street).

Cozy PET-FRIENDLY 1 bd cabin w/ indoor fireplace

Welcome to Castlewood Cabin in the beautiful Whispering Pines community on Cobb Mountain. Wrapped in a forest of pine trees, this rustic, refinished cabin offers one bedroom and one bathroom as well as a fold out sofa in the living room. With room for up to 5 guests this cabin is the ideal spot for a romantic couples getaway, a family road trip or even a small group of friends. Come enjoy all that Lake County has to offer - hiking, biking, boating, fishing, wineries, casinos Harbin and more!

Little Falling Water - Mid-Mod Masterpiece

We invite you to experience the exceptional mid-century modern style and mountain tranquility of Little Falling Water. Set beside a waterfall and built literally over a stream, this architecturally significant residence completed in 1961 was inspired by Frank Lloyd Wright's iconic home of the same name. Walls of glass frame treetop views and the soothing sounds of cascading water surround you on all sides. Decorated with taste, curated for your comfort, close to fine wineries, come enjoy!

Cozy Mountain Retreat | Peaceful with Scenic Views

Get away from it all and enjoy the peace and quiet of Loch Lomond. Relax on the deck surrounded by oaks, grill your favorite meals, and unwind in comfort. The kitchen is fully stocked for cooking, and there’s a small gym area for yoga or stretching. Each room has a comfy queen bed and mini-split A/C and heating. Kick back in the spacious TV room with a wet bar and a desk for remote work, plus fast WiFi to stay connected. Perfect for a peaceful retreat, remote work, or a mountain adventure.

Casa Loco

Experience tranquility at Casa Loco, a serene retreat on 20 picturesque acres in Piner Valley. Perfect for families, this home is a short drive to Middletown, Harbin Hot Springs (10 min), and numerous local wineries. Enjoy bird watching, scenic views, and watch for the luxurious Lotusland resort and Coore & Crenshaw golf course. Explore nearby attractions like the Guenoc/Langtry Farms Winery, Calpine Geothermal Visitor Center, and stunning hiking trails. Book now for a peaceful getaway!

Top of the World View of Clear Lake and Mountains

If you’re looking to getaway, this home high in the hills surrounding beautiful Clear lake, is the retreat for you! Enjoy panoramic views of the lake and mountains. Very quiet, the perfect stop between the redwood trees and the Bay Area Relax on the deck shaded by mature oak trees and watch the osprey’s gliding below you or use the house as a jumping off point. Mendocino National Forest, just 20 minutes away, offers endless possibilities: mountain bike and explore the local trails

Well House

This comfortable cottage is an awesome place to have some quiet, privacy and fun together. It is surrounded by a privacy fence, from my home. The bedroom area is new, and connected by a porch to an older bathroom and kitchen. You can recline in the double recliner leather love-seat and watch a movie on the flat screen television and walk to the stores and restaurants. Three miles from Harbin Hot Springs, and a 20' drive to Calistoga. All races, folks, and LGBT friendly.

Lakeview Cottage A (No cleaning fee)

DISCOUNT: BOOK 4 days or more (message me first and I’ll send you an offer) (Kitchen area) has low ceiling. Approximately 6’3” AIRBNB kitchen rules: leave the kitchen the way you found it or don’t use it. 150 sf deck with spectacular views of the lake. Lots of hummingbirds, wild turkeys, deer, squirrels etc. There is a futon in the living room with Linens available in bedroom County of Lake charges an occupational tax of 11.5%. Which is added to your total.

Countryside Cottage

Escape to our charming countryside oasis near the beautiful Mayacama mountain range. This small, comfortable house offers the perfect getaway just a short drive from the renowned Harbin Hot Springs. Located only 2 minutes from Twin Pine Casino. Whether you're planning a romantic couples getaway, a memorable family vacation, or a fun-filled trip with friends, our cozy haven provides the ideal setting. Book your escape now and experience the countryside.